Hydrochloric Acid → 1-Cyclopentyl-2-phenylethan-1-one

Temperature

-50 °C

To a solution of titanium(IV) isopropoxide (5.13 mmol, 1.46 g) in anhydrous tetrahydro-furan (10 mL) was added a solution of cyclopentylmagnesium chloride in THF (7.69 mmol) at −78° C. Reaction was warmed to −50° C. in 5 min, then maintained at that temperature for 8 min and reaction became dark-brown to black. After cooling back to −78° C., 2-phenylacetonitrile (600 mg, 5.13 mmol) was added by a syringe, and the mixture was stirred at −78° C. for 2 h. 1 N HCl aqueous solution was added to quench the reaction. The mixture was extracted with acetic acid ethyl ester (40 mL) for three times, the combined organic layer was washed with brine (30 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography to give Intermediate 91 (320 mg, yield: 66.5%) as light green oil.

1. customReaction
2. temperaturemaintained at that temperature for 8 min
3. customreaction
4. temperatureAfter cooling back to −78° C.
5. customto quench
6. customthe reaction
7. extractionThe mixture was extracted with acetic acid ethyl ester (40 mL) for three times
8. washthe combined organic layer was washed with brine (30 mL)
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. customThe residue was purified by silica gel column chromatography

ORD record

ord-b1eed6d61db74f0ea9db12da26cad128

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741915B2